Alexei Popyrin's impressive progress on the clay in his breakthrough season was halted rudely by Italian qualifier Gianluca Mager at the Serbia Open in Belgrade while John Millman's difficult season suffered another setback.
Popyrin cut a frustrated figure as he went down 7-5 6-2 to Mager after one of his most disappointing matches in recent weeks on Thursday, a few hours after Millman had given up a one-set lead against Japan's Taro Daniel before losing 3-6 6-2 6-3.
Popyrin has been one of the big success stories of the year for Australian tennis with his victory over David Goffin the Australian Open, his maiden ATP tournament triumph at the Singapore Open and an overall 13-5 record for the season going into the match against Mager.
But just when he was sniffing the prospect of another quarter-final appearance after enjoying a couple of promising wins on clay this season, he looked all at sea on the dirt against the Italian, who outplayed him for much of their 84-minute duel.
Popyrin couldn't get his big serve operating efficiently, with his first delivery percentage down at 54% and Mager was quick to capitalise as he continued his fine run, having come through qualifiers.
Millman had hoped his season could be on the upturn after he'd won only his fourth match of the season in the opening round in Belgrade and things had looked promising as he battled out the first set against Daniel, dominating most of the long, grinding rallies.
But Millman, ranked 83 places ahead of the Japanese, began to be pushed back as Daniel took a more aggressive approach and took the initiative, eventually prevailing after two hours 13 minutes of slog.
"We play a very similar game, solid from the baseline and it was a game of who could pressure more," said Daniel. "I was able to keep pushing until the end."
Daniel was amazed to be playing at all after he had actually lost in the final round of qualifying to Popyrin's conqueror Mager but he got in to the draw as a 'lucky loser' and could hardly credit that he'd ended up making his first tour-level quarter-final for two years.
"It feels great, especially since I came in as a lucky loser," he said in an on-court interview. "The day I lost [in the qualifiers] I had two beers and I was lifting weights in the gym here.
"And then suddenly, 'Okay, you go on court in 10 minutes.' I was surprised."